Author: johnafein

I'm John Fein, Managing Director for Techstars in Kansas City. I love working with entrepreneurs. I also love Boston sports teams and playing the drums.

Why I Don’t Say “Pass” to Founders

I make a point to avoid using the word “pass” when telling founders their startup isn’t a fit for Firebrand. Maybe it’s because I was a founder – I can’t help but feel empathy for them. It’s a key part of our approach. And that word just feels cold and impersonal to me. I don’t even like using it when talking with other investors.

I meet with so many entrepreneurs who pour their blood, sweat and tears into their startup. Though many loathe fundraising they put in the work and try to prepare for rejection while hoping for a Yes. These days there are more investors than ever but the balance of power is still firmly in the hands of VCs. This means for every 100 startups that pitch an investor, they may invest in one. That’s a lot of of No’s.

I totally get that rejection is a big part of fundraising and a thick skin makes it easier, but that doesn’t mean it’s easy for founders to hear “no” over and over again. Especially first-time founders. From some investor responses it can be hard to distinguish “not a fit for us” from “your startup sucks and therefore so do you!”

A few years ago a founder I know showed me a response from a VC he had pitched via email. The founder had gone through all the right steps – researched the investor to ensure he invested in his space and stage, got a warm intro, emailed a concise description of what they did and why he thought it was a fit, and asked if he’d like to meet for coffee or chat on the phone.  The investor’s email reply had one word: Pass.

It’s an extreme example but that stuck in my head and when I started Firebrand I swore I’d never be that kind of VC. I never forget these are human beings I’m dealing with, not deal flow metrics for my LPs. Don’t get me wrong: I’m very clear when we choose not to invest in a startup and strive to give the answer as quickly as possible. And I always provide the reasons when it’s not a fit.

I’m sure plenty of founders and VCs don’t have a problem with the word “pass”. And I certainly don’t judge other investors for using it. My personal experience with it just created a negative association. Founders are the whole reason I have a job and this business process of fundraising happens to be a very personal one. I tell lots of founders their startup isn’t a fit for us, and why, but I don’t use the word “pass”.

I’d love to hear from the founders out there: How does it hit you when an investor says they’re going to “pass” on your startup?



3 Ways to Make Investor Updates Transparent & Effective

You’re about to hit Send on your latest monthly update to your existing investors. And you’re feeling pretty great about it. It includes all of your company’s latest achievements – you even highlighted a few of them with little thumbs-up emojis. With any luck you’ll get several of those “keep up the awesome work” replies – instant dopamine rush!

But wait – before you click Send ask yourself: are you giving your investors the whole story? What about your company’s struggles?

Some founders tend to withhold bad news from their investors because they’re afraid of the reaction: the investors may be mad or disappointed, think less of the team or even pass on investing in the next round. Here’s the thing: existing investors want *all* the updates – the good, the bad and the ugly. As shareholders they deserve that transparency. Also, hiding or sugar coating bad news often prevents investors from helping the company with its biggest needs until it’s too late.

Including these three sections make your investor updates honest and actionable:


A complement to Highlights, Lowlights tell investors what the company is struggling with. Don’t sugarcoat or be dramatic – just tell it like it is. These could include things like falling short of the revenue plan, losing a key team member, or longer than expected sales cycles. Include enough detail so investors are 100% clear what the struggles are. And they’re a great segue to …


As CEO it’s your job to tell your investors what you really need help with. Include at least 2-3 well defined Asks in every update. These could be connections to potential customers or partners, advice on sales strategy, or referrals to key hires. Make them as specific and actionable as possible. Welcome the assistance with open arms!

Financial Snapshot

No matter what the update is, the context is very different if you have thirteen months of runway vs. three. Keep it simple by listing Cash on Hand, Current Burn Rate, and Runway. Runway should be bold and highlighted in red if it’s 6 months or less. If you’re afraid investors will be mad there’s only 5 months of runway left, imagine how they’ll feel when they find out at the last minute it’s almost zero!

Full transparency trumps optimism when it comes to communicating with your stakeholders. If your updates are all sunshine and rainbows your investors will be skeptical anyway. Including Lowlights, Asks, and the Financial Snapshot in every investor update tells the whole story. And being honest about your struggles usually makes your investors want to help you even more.

Now instead of your investors replying with “keep up the awesome work”, they can provide real suggestions to help your business. Less dopamine rush, more chance for long term success!

The Arrogance Fallacy

Words matter. Which is why I mentally cringe when some VCs say they want their founders to be arrogant. Let’s look at two definitions of arrogant:

Merriam-Webster: exaggerating or disposed to exaggerate one’s own worth or importance often by an overbearing manner; showing an offensive attitude of superiority. making claims or pretensions to superior importance or rights; a sense of superiority, self-importance, or entitlement.

Exaggerating. Overbearing. Offensive. Self-important. Entitled. Some VCs probably saw a few of these founders generate huge returns and concluded that’s the CEO blueprint for success. 

Except it’s not.

Arrogance can look like strength and confidence but it’s typically the opposite: a psychological defense mechanism that projects a facade of superiority to hide some serious insecurities. Loud, arrogant people are often the most insecure and fearful people in the room. They are terrified others will think they’re dumb and incompetent. So they overcompensate. The more fame and fortune they attract, the more fearful they become, the more superior and entitled they act. Often with disastrous results. 

We’ve all seen it: one well-funded, arrogant CEO after another, doing offensive and illegal things, falling from grace and sometimes taking their companies with them. 

As a group, VCs themselves aren’t exactly poster children for humility. Worse, arrogance has no doubt played a role in the disgusting culture of sexism and harassment in Silicon Valley. The initial denials and subsequent pseudo-apologies of some offenders were almost too arrogant to believe. 

Arrogance is also related to the shameful lack of diversity among founders that get funded. VCs need to look beyond the arrogant white dudes to fund more women and people of color who don’t fit their preconceived founder image. This is starting to change but there’s much work to be done, by all of us.

Some of the smartest, most confident and successful people I know are actually humble. But don’t confuse humble with meek. They’re outspoken at the right times, stubborn even. But they’re not the loudest – they listen more than talk. They realize there’s a ton they don’t know and they’re honest about it. They operate from a place of relentless learning. They’re smart enough to know it’s not about proving they’re the smartest in the room. 

We shouldn’t be encouraging arrogance in anyone, especially our future business leaders. Let’s be vocal about supporting entrepreneurs who are coachable. Honest. Audacious. Respectful. Persistent. Emotionally intelligent. 

Because those are the qualities of great leaders and human beings. And because words matter. 

Startup Community Spotlight: Cincinnati


The Cincinnati startup community may not be mentioned in the breath as Boulder or Austin – yet – but it’s a well rounded and underrated ecosystem. I recently traveled there to lead a “Group Therapy” event at Union Hall. My friends at Cintrifuse brought 15 founders together with myself and Brad Zapp, Managing Partner at local fund Connetic Ventures. The founders were super engaged and asked great questions about raising capital in the Midwest, bringing on co-founders, and scaling.

After the group therapy session and catching up with awesome Cintrifuse CEO Wendy Lea, I attended a startup happy hour at Connetic’s office where I reconnected with local founders from companies including CompleteSet and FamilyTech. Afterwards Brad and his business partner Kyle took me out for a great dinner at Jeff Ruby’s Steakhouse which turned turned into a long night of eating, drinking and talking – not just with them but also a steady procession of their friends who stopped by to chat.

It was my third visit and like my previous trips I was impressed with the quality of startups I met, the buzz of energy inside Union Hall, and everyone’s hospitality. They’ve been deliberate in building out their ecosystem with some very enviable resources:

Union Hall – It’s been called the “center of gravity for entrepreneurs” and it’s easy to see why. It’s home to Cintrifuse, nationally ranked accelerator The Brandery, one of the Midwest’s most active funds CincyTech, as well as co-working and events.

Cintrifuse – A vital resource for both startups and big corporations, Cintrifuse is many things: education, coworking, connector, fund of funds. Wendy Lea was the driving force in bringing the Techstars FounderCon conference to Cincinnati last year, marking the first time it was held in a city without a Techstars program.

Investors – CincyTech, Connetic, Vine Street Ventures, Queen City Angels, and others I’m sure I’m forgetting. For a community their size they have an enviable array of experienced investors.

Accelerators & Incubators – The Brandery, UpTech, Ocean, and others including Aviatra (formerly Bad Girl Ventures) and HCDC.

Universities – Innovative and engaged universities are essential for any startup ecosystem. Theirs include the University of Cincinnati, Xavier, Miami U., and NKU.

Corporate Engagement – Other communities can learn from how they’ve successfully engaged large companies such as P&G, Kroger, American Financial Group, Cincinnati Bell, and many others.

Identity – Cincinnati is known for CPG, marketing, and branding companies. The startup community itself has built their own brand, StartupCincy, complete with its own website, Twitter and Facebook accounts, and swag. The #StartupCincy hashtag is prevalent on Twitter.

Midwest Benefits – Like other Midwest communities, Cincinnati has that wonderful combination of low cost of living, friendly, welcoming people, and excellent support organizations. The interactions are genuine and not transactional – I feel like the relationships I’ve built there are real and lasting.

Cincinnati has become a special startup community for Firebrand and me. Brad Feld‘s book Startup Communities describes the “leaders” and “feeders” that participate in successful ecosystems – Cincinnati has many already in place. Even better, the people making it all happen are doing it for the right reasons and use the “Give First” approach. I’m very excited to continue supporting them as their ecosystem flourishes in the Midwest.

Just Build It!

I recently got a question from an aspiring entrepreneur trying to figure out the right steps for starting his tech company. He seemed very deliberate about taking the correct approach. He’d been thinking about his idea for two years, staying updated on his market and getting feedback from various sources including two top accelerators.

He said he was moving towards building their MVP but first wanted to know what’s most important to investors about a go-to-market strategy. For example, should he target a niche market first or go after a larger market right away?

Here’s my response to him, with some minor changes from my original text:

  • Don’t build your business for investors
  • Build your business to enable maximum growth in the next 1, 5, 10 years
  • You said you’ve had the idea for two years and watched the market evolve. Markets will continue to evolve. Have a thesis for what direction your market will go but START NOW. If you really want to build a startup you need to just start BUILDING. Perform small experiments along the way, make mistakes, learn from them, and adjust accordingly.
  • I’m not necessarily telling you to quit your job and just go for it with no funding or market proof. Build it in your spare time if you need to. Plenty of successful companies start that way.
  • Starting out in a niche market is fine as long as you have a plan to dominate that niche and then expand into larger markets or additional segments
  • You’ve already gotten feedback from two legit orgs I know – take what feedback makes sense and make it part of your initial strategy
  • A startup isn’t a linear line from beginning to success. It’s a messed up, twisty, jumbled path that’s filled with mostly frustrating, humbling experiences interspersed with a win or two if you’re both good and lucky.
  • Make sure you’re solving a massive pain point. Not a mild headache, a huge migraine. Get some feedback from potential customers to validate this. If the feedback doesn’t validate it, maybe you need to change your idea.
  • Strive to be 10x better than any other solution to the migraine you’re solving
  • Feedback is critical but investors shouldn’t determine your go to market strategy. Think about investors when you’re putting your investor materials together (pitch deck and exec summary). Have a super compelling story, exceptional team, and hopefully some early revenue traction or at least an awesome MVP. These days it can be hard to raise capital for ideas unless you have a stellar track record.

The main point is: Just Build It! Yes you need to research your market, competition, and customers. Do it quickly. And once that feedback validates your thesis, build it! Then get feedback on what you’ve built, iterate and keep building. That’s what entrepreneurs do!

Firebrand Kicks Off 2017 with a Bang!


We’ve had a busy 2017 at Firebrand Ventures and the year is only 24 days old!

First we announced tech pioneer Brian McClendon joined the Firebrand team as advisor. Brian grew up in Lawrence, KS, went to KU, and eventually founded Keyhole whose main product became Google Earth after Google acquired them in 2004. As their VP of Engineering Brian went on to lead the development of Google Maps, Street View, and Earth for almost 11 years before joining Uber in 2015 as their VP of Maps. Although he’s based in SF he frequently visits Lawrence. Brian is an awesome addition to the world class team we’re building.

Then we finalized a partnership with the University of Missouri-Kansas City. Universities should be the primary feeder of talent and tech into any great startup ecosystem. I’ve gotten to know the great folks at UMKC and they want nothing more than to help their entrepreneurs succeed. We can’t wait to invest in exceptional student entrepreneurs right here in KC!

Finally we announced our investment in Des Moines-based Dwolla. Every investment we make is special. Right off the bat this one was special because I’ve known Ben for about 5 years. Dwolla was also the first Midwest startup I engaged with after reconnecting with the regional startup community in 2012. I’ve always respected the culture of building he created there and the scope of their mission. The fact we got to co-invest alongside top tier VCs such as Foundry Group and Union Square Ventures made it even more appealing. To top it off, Brad Feld has been a valued mentor for me so doing a deal together was fantastic.

As for the rest of 2017, I don’t know what other news we’ll have to share but I promise to continue doing everything I can to help founders all over the greater Midwest!

Why I’m So Excited about the Firebrand Ventures-Plexpod Partnership


My new venture fund Firebrand Ventures and KC-based coworking company Plexpod recently announced a partnership. The Plexpod Westport Commons (PWC) space will be the biggest coworking facility in the world! It’s also adjacent to Westport, a vibrant KC entertainment district. Here are some of the reasons why I’m so excited about this partnership:

Providing Key Programming and Access

It’s often hard for entrepreneurs to find high quality, in-person content that can directly help their startup. I’m going to take the best content I’ve curated from my experiences as an entrepreneur and investor and provide it to the companies at PWC. These will include talks, workshops, and panels. I’ll deliver some of it, and will also bring in other experienced folks. Programming will be delivered to additional Plexpod locations too.


During my 25+ year career I’ve learned how valuable mentorship is. Most successful entrepreneurs have had mentors and advisors to help guide them. I’m gotten to know many fantastic mentors through programs like Techstars and look forward to connecting them with Plexpod companies.

Being a Visible and Accessible Investor

I’ll be based at PWC so it’ll be home base for Firebrand Ventures. One of the values that makes Firebrand different is our pledge to be accessible and visible to founders. What better way to demonstrate this than work from the world’s largest coworking space? Plus as a former founder myself I really enjoy being around entrepreneurs!

And Yes, Investments

A natural result of building relationships with founders is I’ll want to invest in the ones that meet our criteria in a very compelling way. I’ve talked and written about how critical it is for entrepreneurs and investors to build real relationships, and I’m really excited to get to know plenty of founders at PWC.

An Ecosystem within an Ecosystem

Anyone who’s read Brad Feld’s Startup Communities knows it takes several types of participants working together to create a well functioning startup ecosystem: entrepreneurs, universities, government, investors, mentors, service providers, and corporations. Just as the greater KC startup community is making progress engaging these different participants, the sheer number of companies working from PWC makes it an ideal place to bring all these parties together. It’s a mutually beneficial dynamic so all participants will get something great out of it, especially when using the “give first” approach.

Startup Density!

Startup density is critical to building a great startup ecosystem. In this case startup density is defined as having a large concentration of startups in a physical area. A central coworking space or neighborhood is key – just look at Boulder (downtown/Pearl St.), Chicago (1871), and Austin (Capitol Factory). The KC startup community has been fairly spread out with pockets of activity in the Crossroads, Startup Village and even Overland Park. PWC will quickly become that central hub our community needs to take it to the next level.

The Bubble of Support

When you get a group of hustling founders working in close proximity they often start helping each other in meaningful and unexpected ways. I’ve seen this first hand while running Techstars programs. Just as community is key to the Firebrand Ventures platform, this spirit of collaboration and “give first” will be hallmarks of PWC.

A Big Milestone

I’ve visited many startup communities across the U.S. and Plexpod Westport Commons is a very big deal for Kansas City and the Midwest. David Brain (SDP) and Gerald Smith (Plexpod) made it happen. As I got to know David and Gerald it became clear we all share a passion for building our community through action and collaboration.

The past four years have seen great advances for Kansas City including Google Fiber, the Startup Village, Techstars, and the Smart City initiative. Plexpod Westport Commons is the next big milestone and I’m proud to be a part of it!

The Right Kind of Coachable

You often hear about the importance of founders being “coachable”, but what does that mean? Does it mean they should follow advice from anyone who seems more knowledgable? Bryce Roberts blogged about being coachable not malleable. A CEO needs to view feedback like any data that’s relevant to their startup: it should be quickly analyzed, filtered, and acted upon only if warranted. CEOs please always remember: it’s your business. If you try to follow everyone’s advice, your business won’t exist very long. At the same time, you should be open to quality advice. So what’s the right kind of “coachable”?

1) First: Be Open to Direct Feedback

Sounds easy, right? Turns out it can be difficult to hear someone call your baby ugly. The trick is to listen, ask relevant follow up questions, and avoid debating. And listen some more. If you’ve met with 25 potential mentors and dismissed every piece of feedback, you probably weren’t open to it in the first place. Keep an open mind and don’t take it personally.

2) Filter the Feedback

Expect conflicting advice from different mentors. At Techstars we call this “mentor whiplash”. You shouldn’t try to follow all of the advice – that would be a mess – but nor should you dismiss it all. Filter it, and hopefully what’s left is actionable advice that sets your startup on the right path. Sometimes you’ll have data and objective advisors to guide you; other times you’ll have to trust your gut. Analyze it, take control and set a definitive direction.

3) Nurture a Continuous Feedback Loop

Great mentors are magic, and once you engage them the best thing to do is keep them engaged. The mentor-mentee relationship is like any other: it needs to be nurtured and it’s up to the mentee to do that. Meet regularly and continue to ask for feedback. I love it when I talk to CEOs who went through Techstars five years ago and still meet with their lead mentors every month. Again, it doesn’t mean you should act on every bit of advice – they’re all data points – just listen and be judicious.

Being coachable isn’t enough – it’s important to be the right kind of coachable. You can be strong and confident while soliciting advice, it just takes practice. Your startup will thank you.

Those 3 Little Words I Love to Hear: “I don’t know.”

Hey startup founders, let me save you the suspense: you don’t know everything. You never will. And no reasonable person expects you to. Even when you’re talking to investors, customers, or partners. 

Yes you should be as knowledgable about your business as humanly possible. You should research the hell out of every scrap of study, article, blog post, speech, interview and tweetstorm relating to your technology, market and competition. But invariably there will be questions you don’t know the answers to. What should you say if someone asks you?

“I don’t know.” That’s what you should say. Be honest. It’s okay. 

Of course, it’s always good to follow it up with a qualifier. If it’s a question about a fact, it’s usually good to say something like “… but I’m going to find out and I’ll let you know as soon as I do.” (Note the “I” in the qualifier vs. delegating it to someone else.) If it’s a question about one of the million future scenarios that may or may not occur in your market, then maybe “… but thanks for bringing that up. I hadn’t considered that but will give it some thought and get back to you.” Then do that. 

Now you’re thinking: “I can’t say that! It’ll make me sound weak, stupid, like I’m a bad founder!”

No it won’t. It’ll make you sound honest and interested in figuring out the answer. 

If instead of saying “I don’t know” you try to wing it with an answer on the spot, how do you think you’ll sound? Probably somewhere between bad and barely mediocre. 

In this age of false-confident, self-promoting “experts”, it’s the honest, humbly confident, and curious that stand out as quality leaders. Investors, customers, and partners want to have faith in you. Be as informed as you possibly can all the time – don’t ever cut corners on that. But admitting you don’t know something shows integrity and also real confidence. Saying you’re interested in figuring it out shows curiosity. Those are a hell of a lot better than bluster and bullshit. 

(For more on the relationship between confidence and competence, see an awesome Brad Feld post here.)

I’d much rather invest in a founder that is confident enough to say “I don’t know” once in a while. Because admitting you don’t know everything really shows you know something. 

Unlock the Magic of Mentors

Teamwork and Leadership with education symbol represented by two human heads shaped with gears with red and gold brain idea made of  cogs representing the concept of intellectual communication through technology exchange.

Startups are hard. Challenges and obstacles are everywhere and founders need all the help they can get.

But what if there were people that wanted to help? People with hard-earned experience who wanted you to learn from their mistakes. Because they love helping startups, no strings attached. Sounds amazing, right?

That’s the magic of mentors! And every founder should have them. At Techstars, our programs are 100% mentor-driven. Each program has 80-100 mentors and we push our companies to identify several program mentors who can spend at least an hour per week with them. I love talking to Techstars alumni who still meet regularly with their program mentors years after graduating from Techstars.

So how can you find amazing mentors and what should you look for?

First: Know What You Need Help With

Make a list of the top areas you need help with. For example: fundraising, marketing, product development, or distribution. Then seek out experts in those areas. Be targeted rather than seeking general business advice.

What To Look For in a Mentor

Great mentors advise startups just because they love to help. They don’t start the conversation by asking how much equity they’ll get. Techstars has this really cool list called the Mentor Manifesto. It’s a set of values and characteristics we want our program mentors to have. Here are a few:

  • Expect nothing in return (you’ll be delighted with what you do get back)
  • Be responsive
  • Clearly separate opinion from fact
  • Guide, don’t control
  • Provide specific actionable advice, don’t be vague
  • Be challenging/robust but never destructive

Where To Find Amazing Mentors

Be proactive and put yourself out there! Start with your network. Get warm intros whenever possible. One method is to connect with fellow entrepreneurs who are at least 2-3 years ahead of you. Some experienced investors can be great mentors, separate from any investing. Also, don’t be shy about reaching out cold to potential mentors if you have some things in common – industry, hobbies, even where you went to college. Anything that can be a foundation for a potential relationship.

Where should they be located?

Technically they can be anywhere and Skype with you, but I’m a big advocate of having local mentors whenever possible. There’s just no substitute for grabbing a coffee or beer every week or two.

How to initially engage mentors 

It’s easier than you think. Simply reach out and say you’re looking for feedback on “x” (something in their wheelhouse) and ask them to grab a coffee or beer. Don’t ask them to be a mentor right away. Meet with them a few times. If after that you have a great connection and think they’d be an amazing mentor for you, ask if they’d be open to meeting on a regular basis.

Don’t pursue someone just because they’re a big name. Find someone who can give their time and provide you with relevant, specific advice. Mentors are for you and your business, not for PR purposes.

How to build the relationship 

Keep meeting and sending updates! It’s up to you to keep the relationship going. Ideally, set a recurring time to meet. Continue to have specific asks. Mentors are usually very busy people – don’t let it go cold!

How many mentors do you need?

I get this question a lot. At Techstars we recommend 2-3 “lead” mentors as the sweet spot. However many it is, you need enough time to meet with them every 1-2 weeks. Each should bring something different to the table. Don’t collect mentors; be choosy and strategic.

How it might evolve

Over time, a mentor may continue on as your mentor; you could add them as a formal advisor; they may invest in your company; and sometimes the relationship becomes reciprocal.

Great mentors are invaluable to founders and can make the startup journey a lot less painful. They can be part business advisor, sounding board, and counselor. The best ones last a lifetime. Once you unlock the magic of mentors you’ll wonder how you ever got by without them!